Carbon Dioxide → HCID 68861511, compound

HRID 2099131Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]2[C:19]3=[C:20]([CH2:22][CH2:23][CH2:24][N:18]3[CH:17]=[C:16]([C:25]([O:27]CC)=[O:26])[C:15]2=[O:30])[CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+:32].C(=O)=O>O1CCCC1>[Na+:32].[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]2[C:19]3=[C:20]([CH2:22][CH2:23][CH2:24][N:18]3[CH:17]=[C:16]([C:25]([O-:27])=[O:26])[C:15]2=[O:30])[CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 9-(3-tert-butoxycarbonylamino-propyl)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate (240 mg, 0.59 mmol) was dissolved in tetrahydrofuran (3 mL) and treated with 2N aqueous sodium hydroxide (0.32 mL). The solution was heated to 50° C. overnight then treated with excess solid carbon dioxide. Evaporation of the solvent gave the title compound as a beige solid. ESMS m/z 387 (MH+). NMR (DMSO-d6) δ 8.83 (s, 1H), 8.11 (bs, 1H), 7.99 (s, 1H), 7.57 (s, 1H), 6.89 (bt, 1H), 4.41 (bt, 2H), 3.04 (t, 2H), 2.94 (q, 2H), 2.71 (t,2H), 2.13 (m, 2H), 1.74 (m, 2H), 1.37 (s, 9H).

Workup

customEvaporation of the solvent

Sources & evidence

ORD record: ord-466c10590e5b468d8bf9bb8adf92103f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569550B2

Reaction notes

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